Before the end of the year, there are eight items we recommend you review: 

• Retirement contributions
• Investment gains and losses
• Charitable giving
• Required minimum distributions
• Healthcare accounts
• Estate plan & Beneficiaries
• Insurance coverage.

Starting a review process in the fall gives you more time to evaluate your options, coordinate with your financial and tax professionals, and complete transactions before applicable deadlines.

This is especially important if you have accumulated $500,000 or more in investable assets; these decisions may be interconnected. For instance:

• Selling an investment can change your taxable income. 
• A Roth conversion may affect your tax bracket and future required distributions. 
• A charitable gift could influence which assets you sell or retain. 
• An outdated beneficiary designation may override instructions in your will.

At Sherr Financial Associates (SFA), our Boston financial planning team views year-end planning as more than a checklist. It’s an opportunity to examine how the different parts of your financial life work together. 

The following eight-year-end financial moves can help you identify questions to discuss with your financial advisor, accountant, estate attorney, and insurance professionals.

Read our latest Quick Guide: What Financial Planning Should You Do This Fall?

Why should you begin year-end financial planning in the fall?

Starting year-end planning in the fall gives you more flexibility to gather information, compare alternatives, and complete time-sensitive transactions.

Think of year-end planning like preparing for a flight. If you arrive early, you have time to check your documents, adjust your luggage, and respond to a gate change. If you arrive moments before departure, even a small delay can cause you to miss the flight. Financial deadlines can work the same way.

Some actions require more time to process. For instance: 

• Charitable gifts of appreciated securities may take time to transfer. 
• Retirement-plan contributions may require payroll changes. 
• Required minimum distributions must be processed. 
• Insurance applications can involve underwriting. 
• Estate documents may require meetings with an attorney and signatures from multiple parties.

Beginning in September or October can also give your financial planner and tax professional time to evaluate projected income before the calendar year closes. By December, you may have fewer practical options, even when a strategy still looks useful on paper.

Check out our Quick Guide: “2026 Financial Tips from Boston Financial Advisors”

1. Have you maximized your retirement account contributions?

Review how much you have contributed to your 401(k), 403(b), 457 plan, IRA, Roth IRA, SIMPLE IRA, SEP IRA, or other retirement account.

The goal is not necessarily to contribute the maximum amount to every available account. Your contribution strategy should reflect your cash-flow needs, current tax situation, employer benefits, retirement timeline, and other financial priorities. Before increasing your contributions, consider the following questions:

• Are you receiving your full employer match? Review the matching formula and your year-to-date contributions so you do not leave an available workplace benefit unused.
• Can you make catch-up contributions? Your age and plan rules may allow additional contributions. Confirm your eligibility and payroll elections.
• Should you choose pre-tax or Roth contributions? Pre-tax contributions may reduce current taxable income, while qualified Roth withdrawals are generally tax-free. Consider your current and expected future tax situation.
• Do you qualify for an IRA contribution or deduction? Your income, filing status, and workplace-plan participation may affect your traditional and Roth IRA options.
• Does your business retirement plan still fit? Business owners should review whether their current plan supports their contribution goals, cash flow, employees, and administrative needs.

Your retirement accounts should work together rather than operate as separate savings buckets. Coordinating contribution amounts, account types, taxes, employer benefits, and available cash can help keep your retirement savings strategy aligned with the rest of your financial plan.

2. Does tax-loss harvesting fit your investment strategy?

Tax-loss harvesting involves selling an investment for less than its tax basis and using the realized loss to offset eligible capital gains. If your losses exceed your gains, a limited amount may generally offset ordinary income, while unused losses may be carried forward under current federal rules.

A loss should not be harvested solely to create a tax deduction. The transaction should also make sense within your portfolio.

Suppose one holding has declined but no longer fits your investment strategy. Selling it may create a tax loss while allowing you to reinvest in a more suitable position. By contrast, selling an investment you still want and immediately repurchasing a substantially identical security may trigger the wash-sale rule and defer the loss.

Your review should extend across your household. A transaction in your account could interact with purchases made in your spouse’s account or an IRA. Automated dividend reinvestments may also create complications.

At SFA, tax-efficient investing is considered within the context of your full financial plan. Before making a year-end trade, you should evaluate the tax impact, portfolio allocation, transaction costs, and whether the replacement investment continues to support your objectives.

3. Which charitable giving strategy fits your goals?

If charitable giving is important to you, year-end planning can help you decide what to give, which assets to use, and when to complete the gift.

Common strategies include:

• Cash gifts: Straightforward, although cash may not always be the most tax-efficient asset to donate.
• Appreciated securities: Donating eligible securities directly may allow you to avoid realizing the embedded capital gain, subject to applicable rules.
• Donor-advised funds: You may contribute assets in one year and recommend grants to qualified charities over time.
• Qualified charitable distributions: If you meet the age and account requirements, a direct transfer from an eligible IRA to a qualified charity may count toward your required minimum distribution.
• Bunching deductions: Combining multiple years of intended donations into one tax year may be useful when itemized deductions would otherwise fall below the applicable standard deduction.

Imagine that you own stock worth $40,000 that originally cost $10,000. Selling the stock and donating the cash may create a taxable gain. Donating the shares directly could produce a different tax result. However, eligibility, deduction limits, holding periods, and the receiving charity’s capabilities must all be considered.

Charitable planning should begin with your values, not the potential tax benefit. Your financial planner and tax professional can then help you evaluate how the gift fits your cash flow, portfolio, estate plan, and tax circumstances.

4. Have you addressed your required minimum distribution?

A required minimum distribution, or RMD, is the amount you generally must withdraw annually from certain tax-deferred retirement accounts after reaching the applicable starting age.

An RMD can affect more than your account balance. Because distributions are generally included in taxable income, they may influence your tax bracket, the taxation of Social Security benefits, and income-related Medicare premiums.

Before year-end, confirm that your required minimum distributions have been calculated correctly and completed by the applicable deadline. Because RMDs can affect your taxes, charitable giving, and cash flow, consider:

• Which accounts require RMDs? Traditional, SEP, and SIMPLE IRAs and many workplace retirement plans are generally subject to RMD rules. Inherited accounts may follow different requirements, while Roth IRAs generally have no lifetime RMDs for the original owner.

• How much must you withdraw? Your RMD is generally based on the account’s prior year-end balance and an IRS life-expectancy factor. Although custodians may estimate the amount, you are responsible for taking the correct distribution.

• Can distributions be combined? RMDs must be calculated separately, but certain eligible accounts may be aggregated. An IRA distribution generally cannot satisfy a 401(k) RMD, so confirm the rules before combining withdrawals.

• What have you already withdrawn? Scheduled payments, one-time withdrawals, and qualified charitable distributions may count toward your requirement. Reconcile your records with each custodian.

• How much tax should be withheld? Taxable RMDs are generally treated as ordinary income. Consider your other income and consult your tax professional before selecting a withholding amount.

• Would a qualified charitable distribution help? If eligible, a QCD transferred directly from an IRA to a qualifying charity may count toward your RMD and be excluded from taxable income.

• How will you use the proceeds? You may spend the money, reserve it for future needs, or reinvest it in a taxable account. Base the decision on your cash flow, taxes, investment strategy, and estate goals.

As you can see, RMD planning involves more than meeting a deadline. This is where a Boston financial advisor can provide guidance to ensure your decisions are coordinated with retirement accounts, income needs, taxes, charitable goals, and broader financial plan.

5. Should you review your FSA and HSA balances?

Flexible Spending Accounts and Health Savings Accounts sound similar, but their year-end rules are different.

An FSA is generally subject to a “use-it-or-lose-it” rule, although an employer may permit a limited carryover or grace period. Review your plan documents, remaining balance, eligible expenses, reimbursement procedures, and submission deadlines. If funds may be forfeited, consider whether you have eligible medical, dental, vision, or prescription expenses.

An HSA is different. The balance belongs to you and can generally be carried forward from year to year. If you are eligible, review your contributions, investment allocation, beneficiary designation, and unreimbursed qualified medical expenses.

If your cash flow is sufficient, an HSA can serve both current healthcare needs and longer-term planning. You might pay current medical expenses from cash and retain documentation in case you choose to seek reimbursement later, provided the expenses and distributions satisfy applicable requirements.

Your eligibility may be affected by your health plan, Medicare enrollment, or participation in certain other healthcare accounts. Review these details before contributing.

6. Are your estate documents and beneficiaries current?

Your estate plan should reflect your life today, not your circumstances when the documents were originally signed.

Review your will, trusts, durable financial power of attorney, healthcare proxy, medical directives, and any guardianship provisions. Changes in marriage, divorce, births, deaths, business ownership, real estate, charitable intentions, or state residency may create a reason to speak with your estate attorney.

Beneficiary designations should be reviewed independently from your will. Assets such as retirement accounts, life insurance policies, annuities, and transfer-on-death accounts generally pass directly to the individuals named on the account. Because these instructions may override provisions in your will, confirm that each designation reflects your current wishes.

If you live in Massachusetts, estate planning may require both federal and state-level analysis. The value of a home, retirement accounts, insurance, and other assets can produce an estate larger than you expect.

While we don’t provide legal advice, our financial planners in Boston can help you organize financial information and coordinate planning conversations with your estate attorney and tax professional.

7. Does your insurance still protect the risks you face?

Insurance needs change as your income, family, assets, debts, and responsibilities evolve.

Review your:

• Life insurance
• Disability income insurance
• Homeowners and automobile coverage
• Personal umbrella liability policy
• Long-term care coverage
• Business insurance
• Property and casualty limits

The purpose is not simply to buy more coverage. It’s to determine whether your current policies still align with the risks that could disrupt your plan.

For example, your umbrella liability limit may not have changed even though your assets and income have grown substantially. A life insurance policy purchased when your children were young may serve a different purpose after they become financially independent. A business owner may need to review succession, key-person, or buy-sell funding arrangements.

Think of insurance as the guardrail around your financial plan. It doesn’t determine your destination, but it may reduce the financial impact of an unexpected detour.

Read our new blog: “What to Expect When Applying for Life Insurance.”

How can Boston financial advisors support year-end planning?

At Sherr Financial Associates (SFA), our team brings more than 60 years of combined financial and investment experience to this process. Our approach is personal rather than cookie-cutter. 

We work with you to examine how retirement planning, investment management, tax-efficient strategies, risk management, charitable giving, and estate considerations fit into a single financial framework.

Schedule a call with our team of experienced financial planners today.

Frequently Asked Questions About Year-End Financial Planning

When should I start year-end financial planning?

September or October is often a practical time to begin. Starting in the fall gives you time to collect records, project income, meet with your professional team, and process transactions before year-end deadlines.

What financial decisions must be completed by December 31?

Many actions, including workplace retirement-plan deferrals, tax-loss sales, certain charitable gifts, and required minimum distributions, may need to be completed by December 31. Exact deadlines depend on the account, transaction, institution, and applicable tax rules.

Can tax-loss harvesting reduce my taxes?

Realized investment losses may offset eligible capital gains and, within applicable limits, ordinary income. However, wash-sale rules, portfolio changes, and future tax consequences should be considered before selling.

Should I contribute to a traditional or Roth retirement account?

A traditional contribution may offer a current tax benefit when deductible, while a Roth contribution uses after-tax dollars and may provide tax-free qualified withdrawals. Your eligibility and preferred approach depend on income, tax rates, workplace coverage, and retirement expectations.

How can I make tax-efficient charitable gifts?

Depending on your circumstances, you might consider cash, appreciated securities, a donor-advised fund, a qualified charitable distribution, or grouping multiple years of gifts into one year. Tax rules and deduction limits apply.

What happens if I miss my required minimum distribution?

Failure to take the required amount by the applicable deadline may result in an excise tax. Corrective options may be available, but you should contact your financial and tax professionals promptly.

Do unused FSA funds expire at year-end?

FSA funds are generally subject to use-it-or-lose-it rules, but some employer plans offer a limited carryover or grace period. Review your specific plan rather than assuming the balance will remain available.

How often should I update my beneficiaries?

Review beneficiaries at least annually and after major life events such as marriage, divorce, a birth, a death, or a change in your estate plan. Confirm both primary and contingent beneficiaries.

Do I need a financial advisor if I have $500,000 invested?

Asset level alone doesn’t determine whether you need an advisor. You may benefit from professional guidance if you want assistance coordinating investments, taxes, retirement income, estate planning, insurance, charitable giving, or complex financial decisions.